2-Bromopyridine-4-methanol Chemical Properties

Melting point:

58-61°C

Boiling point:

316.6±27.0 °C(Predicted)

Density 

1.668±0.06 g/cm3(Predicted)

storage temp. 

Keep in dark place,Sealed in dry,Room Temperature

form 

solid

pka

13.06±0.10(Predicted)

color 

White

BRN 

4244047

InChI

InChI=1S/C6H6BrNO/c7-6-3-5(4-9)1-2-8-6/h1-3,9H,4H2

InChIKey

IQNUGAFIKDRYRP-UHFFFAOYSA-N

SMILES

C1(Br)=NC=CC(CO)=C1

CAS DataBase Reference

118289-16-0(CAS DataBase Reference)

Safety Information

Hazard Codes 

Xi,Xn

Risk Statements 

36/37/38-22

Safety Statements 

26-36-37-22

WGK Germany 

1

HazardClass 

IRRITANT

HS Code 

29339900

MSDS

• Language:English Provider:ALFA

2-Bromopyridine-4-methanol Usage And Synthesis

Chemical Properties

2-Bromopyridine-4-methanol is a white to brown powder, it is stable under normal conditions.

Uses

2-Bromo-4-hydroxymethylpyridine is used to synthesize aza- and diazabiphenyl analogs of the antitubercular drug (6S)-2-nitro-6-{[4-(trifluoromethoxy)benzyl]oxy}-6,7-dihydro-5H-imidazo[2,1-b][1,3]oxazine (PA-824). It is also used to N3/8-disubstituted 3,8-diazabicyclo[3.2.1]octane analogues of 3,8-bis[2-(3,4,5-trimethoxyphenyl)pyridin-4-yl]methyl-piperazine with antiproliferative properties.

Health Hazard

Contact with 2-Bromopyridine-4-methanol causes skin irritation and serious eye irritation.

Synthesis

General procedure for the synthesis of 2-bromo-4-pyridinemethanol from 2-bromo-4-pyridinecarboxylic acid: To a solution of tetrahydrofuran (30 mL) containing 2-bromo-4-pyridinecarboxylic acid (2 g, 9.9 mmol, 1.0 eq.) was added drop-wise the boron trifluoride ether compound (4.18 g, 29.7 mmol, 3.0 eq.) at 0 °C. The reaction mixture was stirred at room temperature for 3 hours. Upon completion of the reaction, the reaction mixture was transferred to ice water and the product was extracted with ethyl acetate. The organic layers were combined, washed with brine solution, dried over anhydrous sodium sulfate and concentrated under reduced pressure to give 2-bromo-4-pyridine methanol (1.4 g, 75.21% yield). Mass spectrum (electrospray): m/z 189.65 [M]+.

References

[1] Patent: WO2018/71794, 2018, A1. Location in patent: Paragraph 00983; 00984
[2] Chemical and Pharmaceutical Bulletin, 1990, vol. 38, # 9, p. 2446 - 2458
[3] Journal of Medicinal Chemistry, 1997, vol. 40, # 18, p. 2866 - 2875
[4] Patent: US2005/54654, 2005, A1. Location in patent: Page/Page column 36
[5] Patent: EP2098517, 2009, A1. Location in patent: Page/Page column 32

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